Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100011665/qa0371sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100011665/qa0371Isup2.hkl |
CCDC reference: 152664
The title compound was synthesized according to the literature method of Wu et al. (1997) and recrystallized from dry ethanol. Crystals suitable for X-ray determination were obtained by slow evaporation from a solution in formyl acetoacetate over a period of three weeks.
Data collection: CAD-4-PC (Enraf-Nonius, 1989); cell refinement: CAD-4-PC (Enraf-Nonius, 1989); data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
C22H20O6 | Z = 4 |
Mr = 380.38 | F(000) = 800 |
Triclinic, P1 | Dx = 1.271 Mg m−3 |
a = 8.828 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 15.174 (5) Å | Cell parameters from 25 reflections |
c = 16.420 (7) Å | θ = 10.9–12.8° |
α = 113.52 (3)° | µ = 0.09 mm−1 |
β = 99.27 (4)° | T = 293 K |
γ = 83.53 (4)° | Block, colourless |
V = 1987.6 (17) Å3 | 0.45 × 0.37 × 0.35 mm |
Enraf-Nonius CAD-4 diffractometer | 6310 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.4° |
Graphite monochromator | h = −10→10 |
θ/2θ scans | k = −18→16 |
Absorption correction: ψ scan (North et al., 1968) | l = 0→19 |
Tmin = 0.941, Tmax = 0.966 | 3 standard reflections every 400 reflections |
6828 measured reflections | intensity decay: 0.1% |
6828 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.017 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.058 | H-atom parameters constrained |
S = 0.93 | w = 1/[σ2(Fo2) + (0.032P)2 + 0.140P] where P = (Fo2 + 2Fc2)/3 |
6828 reflections | (Δ/σ)max = 0.002 |
505 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C22H20O6 | γ = 83.53 (4)° |
Mr = 380.38 | V = 1987.6 (17) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.828 (6) Å | Mo Kα radiation |
b = 15.174 (5) Å | µ = 0.09 mm−1 |
c = 16.420 (7) Å | T = 293 K |
α = 113.52 (3)° | 0.45 × 0.37 × 0.35 mm |
β = 99.27 (4)° |
Enraf-Nonius CAD-4 diffractometer | 6828 independent reflections |
Absorption correction: ψ scan (North et al., 1968) | 6310 reflections with I > 2σ(I) |
Tmin = 0.941, Tmax = 0.966 | 3 standard reflections every 400 reflections |
6828 measured reflections | intensity decay: 0.1% |
R[F2 > 2σ(F2)] = 0.017 | 0 restraints |
wR(F2) = 0.058 | H-atom parameters constrained |
S = 0.93 | Δρmax = 0.30 e Å−3 |
6828 reflections | Δρmin = −0.32 e Å−3 |
505 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O11 | 0.00662 (8) | 0.50155 (5) | 0.12518 (4) | 0.07635 (19) | |
O12 | 0.20153 (8) | 0.39634 (5) | 0.08928 (4) | 0.0799 (2) | |
O13 | −0.15387 (7) | 0.49208 (5) | 0.28150 (5) | 0.07019 (16) | |
O14 | 0.29288 (6) | 0.51417 (4) | 0.42116 (4) | 0.05981 (14) | |
O15 | 0.07138 (6) | 0.59348 (4) | 0.45891 (3) | 0.05397 (13) | |
O16 | 0.44367 (7) | 0.51032 (5) | 0.25929 (5) | 0.07042 (16) | |
C11 | 0.12183 (9) | 0.46319 (5) | 0.14712 (5) | 0.05022 (17) | |
C12 | 0.18923 (8) | 0.48043 (5) | 0.23955 (5) | 0.04256 (15) | |
C13 | 0.10007 (8) | 0.52521 (5) | 0.30725 (4) | 0.04064 (14) | |
C14 | 0.16661 (8) | 0.54263 (5) | 0.39989 (5) | 0.04497 (16) | |
C15 | 0.15276 (12) | 0.36875 (9) | −0.00669 (7) | 0.0805 (3) | |
H151 | 0.0607 | 0.4061 | −0.0172 | 0.080* | |
H152 | 0.1327 | 0.3009 | −0.0355 | 0.080* | |
C16 | 0.28599 (15) | 0.39035 (9) | −0.04097 (8) | 0.0929 (3) | |
H161 | 0.2630 | 0.3736 | −0.1044 | 0.080* | |
H162 | 0.3761 | 0.3535 | −0.0290 | 0.080* | |
H163 | 0.3041 | 0.4577 | −0.0115 | 0.080* | |
C17 | 0.12746 (10) | 0.61271 (7) | 0.55240 (5) | 0.0627 (2) | |
H171 | 0.2190 | 0.6493 | 0.5710 | 0.080* | |
H172 | 0.1527 | 0.5528 | 0.5608 | 0.080* | |
C18 | 0.00133 (11) | 0.66939 (6) | 0.60635 (6) | 0.0654 (2) | |
H181 | 0.0344 | 0.6834 | 0.6687 | 0.080* | |
H182 | −0.0886 | 0.6325 | 0.5873 | 0.080* | |
H183 | −0.0225 | 0.7285 | 0.5975 | 0.080* | |
C111 | 0.40709 (7) | 0.35697 (5) | 0.25058 (4) | 0.04054 (14) | |
C112 | 0.56257 (9) | 0.32814 (6) | 0.25347 (5) | 0.05188 (17) | |
H11A | 0.6344 | 0.3707 | 0.2578 | 0.080* | |
C113 | 0.61092 (10) | 0.23801 (6) | 0.25006 (6) | 0.0655 (2) | |
H11B | 0.7148 | 0.2189 | 0.2506 | 0.080* | |
C114 | 0.50469 (11) | 0.17523 (6) | 0.24574 (6) | 0.0661 (2) | |
H11C | 0.5376 | 0.1147 | 0.2455 | 0.080* | |
C115 | 0.35100 (10) | 0.20222 (6) | 0.24180 (6) | 0.0603 (2) | |
H11D | 0.2798 | 0.1594 | 0.2376 | 0.080* | |
C116 | 0.30173 (8) | 0.29194 (5) | 0.24396 (5) | 0.04793 (16) | |
H11E | 0.1972 | 0.3095 | 0.2410 | 0.080* | |
C117 | 0.35294 (8) | 0.45200 (5) | 0.25282 (5) | 0.04772 (16) | |
C121 | −0.11949 (8) | 0.64702 (5) | 0.29435 (4) | 0.04367 (15) | |
C122 | −0.27624 (9) | 0.67151 (6) | 0.28460 (5) | 0.05212 (17) | |
H12B | −0.3474 | 0.6274 | 0.2774 | 0.080* | |
C123 | −0.32579 (10) | 0.76161 (6) | 0.28559 (6) | 0.0611 (2) | |
H12C | −0.4305 | 0.7782 | 0.2803 | 0.080* | |
C124 | −0.22442 (11) | 0.82591 (6) | 0.29404 (6) | 0.0620 (2) | |
H12D | −0.2603 | 0.8856 | 0.2933 | 0.080* | |
C125 | −0.06708 (10) | 0.80406 (6) | 0.30380 (6) | 0.0605 (2) | |
H12E | 0.0023 | 0.8488 | 0.3099 | 0.080* | |
C126 | −0.01497 (9) | 0.71435 (5) | 0.30438 (5) | 0.05078 (17) | |
H12F | 0.0900 | 0.6991 | 0.3115 | 0.080* | |
C127 | −0.06356 (9) | 0.55232 (5) | 0.29246 (5) | 0.04917 (17) | |
O21 | 0.28058 (7) | −0.02632 (5) | −0.02297 (5) | 0.07907 (19) | |
O22 | 0.23038 (5) | 0.13180 (4) | 0.01489 (3) | 0.04960 (12) | |
O23 | −0.02822 (7) | 0.16621 (4) | 0.14567 (4) | 0.06527 (15) | |
C21 | 0.19269 (8) | 0.04491 (5) | 0.00059 (5) | 0.05027 (17) | |
C22 | 0.03379 (8) | 0.04454 (5) | 0.01468 (5) | 0.04837 (16) | |
C23 | 0.38731 (9) | 0.14387 (6) | 0.00614 (6) | 0.05532 (18) | |
H231 | 0.4574 | 0.1040 | 0.0306 | 0.080* | |
H232 | 0.4122 | 0.2104 | 0.0404 | 0.080* | |
C24 | 0.40877 (12) | 0.11695 (8) | −0.08979 (7) | 0.0748 (2) | |
H241 | 0.5142 | 0.1233 | −0.0935 | 0.080* | |
H242 | 0.3437 | 0.1588 | −0.1132 | 0.080* | |
H243 | 0.3822 | 0.0515 | −0.1241 | 0.080* | |
C211 | −0.12743 (8) | 0.19704 (5) | 0.01826 (5) | 0.04716 (16) | |
C212 | −0.19498 (10) | 0.28516 (6) | 0.06529 (6) | 0.0611 (2) | |
H21A | −0.1871 | 0.3079 | 0.1274 | 0.080* | |
C213 | −0.27430 (12) | 0.34027 (7) | 0.02128 (7) | 0.0766 (3) | |
H21B | −0.3196 | 0.3998 | 0.0540 | 0.080* | |
C214 | −0.28707 (12) | 0.30865 (7) | −0.06912 (8) | 0.0788 (3) | |
H21C | −0.3416 | 0.3465 | −0.0979 | 0.080* | |
C215 | −0.21962 (11) | 0.22045 (7) | −0.11912 (7) | 0.0727 (2) | |
H21D | −0.2276 | 0.1987 | −0.1811 | 0.080* | |
C216 | −0.13982 (10) | 0.16535 (6) | −0.07437 (6) | 0.0590 (2) | |
H21E | −0.0938 | 0.1061 | −0.1070 | 0.080* | |
C217 | −0.04359 (8) | 0.13709 (5) | 0.06365 (5) | 0.04819 (16) | |
O31 | 0.34255 (7) | 0.85144 (4) | 0.40777 (4) | 0.06878 (16) | |
O32 | 0.51699 (7) | 0.80945 (4) | 0.50126 (4) | 0.06315 (15) | |
O33 | 0.53995 (7) | 1.00782 (4) | 0.67139 (4) | 0.06577 (15) | |
C31 | 0.44906 (9) | 0.87216 (6) | 0.47036 (5) | 0.05367 (18) | |
C32 | 0.51740 (9) | 0.96528 (6) | 0.51851 (5) | 0.05484 (18) | |
C33 | 0.46692 (11) | 0.71254 (6) | 0.46203 (6) | 0.0653 (2) | |
H331 | 0.4504 | 0.6903 | 0.3973 | 0.080* | |
H332 | 0.3714 | 0.7096 | 0.4827 | 0.080* | |
C34 | 0.59145 (13) | 0.65127 (7) | 0.49072 (7) | 0.0809 (3) | |
H341 | 0.5465 | 0.6007 | 0.4982 | 0.080* | |
H342 | 0.6479 | 0.6901 | 0.5464 | 0.080* | |
H343 | 0.6598 | 0.6237 | 0.4459 | 0.080* | |
C311 | 0.77690 (8) | 0.95936 (5) | 0.61405 (5) | 0.04459 (15) | |
C312 | 0.85644 (9) | 0.92821 (6) | 0.53976 (5) | 0.05626 (19) | |
H31A | 0.8035 | 0.9212 | 0.4839 | 0.080* | |
C313 | 1.01386 (10) | 0.90758 (7) | 0.54853 (6) | 0.0655 (2) | |
H31B | 1.0660 | 0.8863 | 0.4986 | 0.080* | |
C314 | 1.09319 (10) | 0.91872 (6) | 0.63161 (6) | 0.0658 (2) | |
H31C | 1.1992 | 0.9068 | 0.6378 | 0.080* | |
C315 | 1.01562 (11) | 0.94735 (6) | 0.70486 (6) | 0.0646 (2) | |
H31D | 1.0686 | 0.9530 | 0.7603 | 0.080* | |
C316 | 0.85847 (9) | 0.96784 (6) | 0.69610 (5) | 0.05354 (18) | |
H31E | 0.8068 | 0.9876 | 0.7461 | 0.080* | |
C317 | 0.61051 (9) | 0.98141 (5) | 0.60530 (5) | 0.04932 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O11 | 0.0772 (4) | 0.0808 (4) | 0.0586 (3) | 0.0187 (3) | 0.0033 (3) | 0.0221 (3) |
O12 | 0.0768 (4) | 0.1017 (5) | 0.0562 (3) | 0.0255 (4) | 0.0128 (3) | 0.0318 (3) |
O13 | 0.0588 (3) | 0.0666 (4) | 0.0882 (4) | −0.0031 (3) | 0.0075 (3) | 0.0340 (3) |
O14 | 0.0560 (3) | 0.0662 (3) | 0.0536 (3) | 0.0002 (3) | 0.0032 (2) | 0.0218 (3) |
O15 | 0.0526 (3) | 0.0600 (3) | 0.0478 (3) | −0.0009 (2) | 0.0079 (2) | 0.0193 (2) |
O16 | 0.0628 (4) | 0.0685 (4) | 0.0863 (4) | −0.0048 (3) | 0.0135 (3) | 0.0348 (3) |
C11 | 0.0517 (4) | 0.0495 (4) | 0.0498 (4) | 0.0042 (3) | 0.0056 (3) | 0.0218 (3) |
C12 | 0.0437 (4) | 0.0402 (3) | 0.0443 (4) | −0.0026 (3) | 0.0051 (3) | 0.0170 (3) |
C13 | 0.0424 (3) | 0.0376 (3) | 0.0433 (4) | −0.0019 (3) | 0.0060 (3) | 0.0170 (3) |
C14 | 0.0460 (4) | 0.0429 (4) | 0.0466 (4) | −0.0045 (3) | 0.0053 (3) | 0.0176 (3) |
C15 | 0.0760 (6) | 0.0952 (7) | 0.0690 (6) | 0.0172 (5) | 0.0139 (5) | 0.0347 (5) |
C16 | 0.1136 (9) | 0.0933 (8) | 0.0735 (6) | 0.0051 (7) | 0.0103 (6) | 0.0375 (6) |
C17 | 0.0639 (5) | 0.0713 (5) | 0.0518 (4) | −0.0101 (4) | 0.0057 (4) | 0.0216 (4) |
C18 | 0.0728 (5) | 0.0653 (5) | 0.0575 (5) | −0.0098 (4) | 0.0138 (4) | 0.0195 (4) |
C111 | 0.0373 (3) | 0.0452 (4) | 0.0381 (3) | −0.0022 (3) | 0.0043 (3) | 0.0153 (3) |
C112 | 0.0445 (4) | 0.0544 (4) | 0.0543 (4) | −0.0029 (3) | 0.0038 (3) | 0.0195 (3) |
C113 | 0.0517 (5) | 0.0647 (5) | 0.0723 (5) | 0.0070 (4) | 0.0037 (4) | 0.0228 (4) |
C114 | 0.0724 (6) | 0.0554 (5) | 0.0683 (5) | 0.0062 (4) | 0.0051 (4) | 0.0257 (4) |
C115 | 0.0647 (5) | 0.0558 (5) | 0.0640 (5) | −0.0079 (4) | 0.0081 (4) | 0.0258 (4) |
C116 | 0.0448 (4) | 0.0499 (4) | 0.0484 (4) | −0.0007 (3) | 0.0072 (3) | 0.0184 (3) |
C117 | 0.0477 (4) | 0.0497 (4) | 0.0460 (4) | −0.0012 (3) | 0.0068 (3) | 0.0189 (3) |
C121 | 0.0433 (4) | 0.0472 (4) | 0.0408 (3) | −0.0009 (3) | 0.0072 (3) | 0.0172 (3) |
C122 | 0.0471 (4) | 0.0577 (4) | 0.0514 (4) | −0.0020 (3) | 0.0057 (3) | 0.0214 (3) |
C123 | 0.0526 (4) | 0.0665 (5) | 0.0597 (5) | 0.0113 (4) | 0.0098 (4) | 0.0227 (4) |
C124 | 0.0711 (5) | 0.0531 (4) | 0.0609 (5) | 0.0088 (4) | 0.0126 (4) | 0.0227 (4) |
C125 | 0.0673 (5) | 0.0527 (4) | 0.0651 (5) | −0.0076 (4) | 0.0119 (4) | 0.0241 (4) |
C126 | 0.0470 (4) | 0.0507 (4) | 0.0553 (4) | −0.0012 (3) | 0.0084 (3) | 0.0209 (3) |
C127 | 0.0475 (4) | 0.0516 (4) | 0.0477 (4) | −0.0008 (3) | 0.0061 (3) | 0.0191 (3) |
O21 | 0.0561 (4) | 0.0656 (4) | 0.1194 (6) | 0.0039 (3) | 0.0224 (4) | 0.0376 (4) |
O22 | 0.0417 (3) | 0.0498 (3) | 0.0579 (3) | −0.0036 (2) | 0.0076 (2) | 0.0207 (2) |
O23 | 0.0633 (3) | 0.0675 (4) | 0.0635 (4) | 0.0021 (3) | 0.0117 (3) | 0.0241 (3) |
C21 | 0.0425 (4) | 0.0497 (4) | 0.0603 (4) | −0.0003 (3) | 0.0071 (3) | 0.0235 (3) |
C22 | 0.0420 (4) | 0.0503 (4) | 0.0549 (4) | 0.0013 (3) | 0.0083 (3) | 0.0228 (3) |
C23 | 0.0447 (4) | 0.0553 (4) | 0.0671 (5) | −0.0060 (3) | 0.0065 (3) | 0.0244 (4) |
C24 | 0.0701 (6) | 0.0793 (6) | 0.0790 (6) | −0.0064 (5) | 0.0176 (5) | 0.0311 (5) |
C211 | 0.0397 (3) | 0.0464 (4) | 0.0547 (4) | −0.0029 (3) | 0.0066 (3) | 0.0186 (3) |
C212 | 0.0631 (5) | 0.0526 (4) | 0.0642 (5) | 0.0010 (4) | 0.0125 (4) | 0.0187 (4) |
C213 | 0.0783 (6) | 0.0607 (5) | 0.0892 (7) | 0.0105 (5) | 0.0191 (5) | 0.0279 (5) |
C214 | 0.0738 (6) | 0.0716 (6) | 0.0955 (7) | 0.0012 (5) | −0.0007 (5) | 0.0427 (6) |
C215 | 0.0730 (6) | 0.0790 (6) | 0.0691 (6) | −0.0008 (5) | 0.0059 (5) | 0.0339 (5) |
C216 | 0.0582 (5) | 0.0545 (4) | 0.0598 (5) | 0.0024 (4) | 0.0061 (4) | 0.0193 (4) |
C217 | 0.0424 (4) | 0.0508 (4) | 0.0510 (4) | −0.0033 (3) | 0.0083 (3) | 0.0183 (3) |
O31 | 0.0687 (4) | 0.0588 (3) | 0.0780 (4) | −0.0026 (3) | 0.0029 (3) | 0.0284 (3) |
O32 | 0.0638 (3) | 0.0553 (3) | 0.0681 (4) | −0.0095 (3) | −0.0022 (3) | 0.0241 (3) |
O33 | 0.0646 (4) | 0.0728 (4) | 0.0608 (3) | 0.0007 (3) | 0.0130 (3) | 0.0261 (3) |
C31 | 0.0492 (4) | 0.0524 (4) | 0.0595 (5) | −0.0062 (3) | 0.0075 (4) | 0.0206 (4) |
C32 | 0.0518 (4) | 0.0544 (4) | 0.0570 (4) | 0.0000 (3) | 0.0096 (3) | 0.0201 (4) |
C33 | 0.0683 (5) | 0.0570 (5) | 0.0709 (5) | −0.0117 (4) | 0.0013 (4) | 0.0256 (4) |
C34 | 0.0870 (7) | 0.0735 (6) | 0.0794 (6) | −0.0071 (5) | −0.0028 (5) | 0.0309 (5) |
C311 | 0.0485 (4) | 0.0392 (3) | 0.0454 (4) | −0.0042 (3) | 0.0029 (3) | 0.0164 (3) |
C312 | 0.0529 (4) | 0.0653 (5) | 0.0502 (4) | −0.0042 (4) | 0.0020 (3) | 0.0235 (4) |
C313 | 0.0608 (5) | 0.0735 (6) | 0.0650 (5) | −0.0006 (4) | 0.0130 (4) | 0.0288 (4) |
C314 | 0.0542 (5) | 0.0669 (5) | 0.0764 (6) | −0.0008 (4) | 0.0001 (4) | 0.0316 (5) |
C315 | 0.0673 (5) | 0.0658 (5) | 0.0592 (5) | −0.0075 (4) | −0.0057 (4) | 0.0269 (4) |
C316 | 0.0614 (5) | 0.0518 (4) | 0.0481 (4) | −0.0069 (3) | 0.0037 (3) | 0.0203 (3) |
C317 | 0.0539 (4) | 0.0454 (4) | 0.0491 (4) | −0.0043 (3) | 0.0083 (3) | 0.0178 (3) |
O11—C11 | 1.1912 (11) | O22—C21 | 1.3156 (10) |
O12—C11 | 1.3082 (12) | O22—C23 | 1.4546 (13) |
O12—C15 | 1.4625 (13) | O23—C217 | 1.2277 (11) |
O13—C127 | 1.2207 (11) | C21—C22 | 1.4590 (14) |
O14—C14 | 1.1990 (11) | C22—C22i | 1.4086 (16) |
O15—C14 | 1.3270 (12) | C22—C217 | 1.4646 (13) |
O15—C17 | 1.4551 (12) | C23—C24 | 1.4996 (14) |
O16—C117 | 1.2219 (11) | C23—H231 | 0.9700 |
C11—C12 | 1.4674 (12) | C23—H232 | 0.9700 |
C12—C13 | 1.3694 (12) | C24—H241 | 0.9600 |
C12—C117 | 1.4681 (14) | C24—H242 | 0.9600 |
C13—C127 | 1.4654 (14) | C24—H243 | 0.9600 |
C13—C14 | 1.4680 (12) | C211—C212 | 1.3727 (13) |
C15—C16 | 1.5017 (18) | C211—C216 | 1.3896 (13) |
C15—H151 | 0.9700 | C211—C217 | 1.4637 (12) |
C15—H152 | 0.9700 | C212—C213 | 1.3781 (14) |
C16—H161 | 0.9600 | C212—H21A | 0.9300 |
C16—H162 | 0.9600 | C213—C214 | 1.3549 (16) |
C16—H163 | 0.9600 | C213—H21B | 0.9300 |
C17—C18 | 1.5026 (15) | C214—C215 | 1.3858 (16) |
C17—H171 | 0.9700 | C214—H21C | 0.9300 |
C17—H172 | 0.9700 | C215—C216 | 1.3879 (14) |
C18—H181 | 0.9600 | C215—H21D | 0.9300 |
C18—H182 | 0.9600 | C216—H21E | 0.9300 |
C18—H183 | 0.9600 | O31—C31 | 1.2397 (12) |
C111—C112 | 1.3921 (13) | O32—C31 | 1.2965 (11) |
C111—C116 | 1.3926 (12) | O32—C33 | 1.4393 (12) |
C111—C117 | 1.4551 (11) | O33—C317 | 1.2411 (11) |
C112—C113 | 1.3678 (13) | C31—C32 | 1.4603 (13) |
C112—H11A | 0.9300 | C32—C32ii | 1.3970 (17) |
C113—C114 | 1.3848 (15) | C32—C317 | 1.4684 (13) |
C113—H11B | 0.9300 | C33—C34 | 1.4991 (15) |
C114—C115 | 1.3712 (15) | C33—H331 | 0.9700 |
C114—H11C | 0.9300 | C33—H332 | 0.9700 |
C115—C116 | 1.3700 (12) | C34—H341 | 0.9600 |
C115—H11D | 0.9300 | C34—H342 | 0.9600 |
C116—H11E | 0.9300 | C34—H343 | 0.9600 |
C121—C122 | 1.3924 (14) | C311—C316 | 1.3857 (12) |
C121—C126 | 1.3970 (12) | C311—C312 | 1.3948 (13) |
C121—C127 | 1.4557 (12) | C311—C317 | 1.4662 (14) |
C122—C123 | 1.3821 (13) | C312—C313 | 1.3868 (15) |
C122—H12B | 0.9300 | C312—H31A | 0.9300 |
C123—C124 | 1.3494 (14) | C313—C314 | 1.3838 (15) |
C123—H12C | 0.9300 | C313—H31B | 0.9300 |
C124—C125 | 1.3899 (16) | C314—C315 | 1.3732 (15) |
C124—H12D | 0.9300 | C314—H31C | 0.9300 |
C125—C126 | 1.3902 (12) | C315—C316 | 1.3842 (15) |
C125—H12E | 0.9300 | C315—H31D | 0.9300 |
C126—H12F | 0.9300 | C316—H31E | 0.9300 |
O21—C21 | 1.2223 (11) | ||
C11—O12—C15 | 119.79 (8) | C21—O22—C23 | 117.89 (7) |
C14—O15—C17 | 116.35 (7) | O21—C21—O22 | 123.47 (8) |
O11—C11—O12 | 122.68 (8) | O21—C21—C22 | 124.85 (8) |
O11—C11—C12 | 125.80 (8) | O22—C21—C22 | 111.68 (7) |
O12—C11—C12 | 111.48 (7) | C22i—C22—C21 | 118.61 (9) |
C13—C12—C11 | 119.09 (7) | C22i—C22—C217 | 123.56 (9) |
C13—C12—C117 | 124.49 (8) | C21—C22—C217 | 117.72 (8) |
C11—C12—C117 | 116.34 (7) | O22—C23—C24 | 111.57 (8) |
C12—C13—C127 | 123.61 (8) | O22—C23—H231 | 109.3 |
C12—C13—C14 | 119.42 (7) | C24—C23—H231 | 109.3 |
C127—C13—C14 | 116.86 (7) | O22—C23—H232 | 109.3 |
O14—C14—O15 | 122.78 (8) | C24—C23—H232 | 109.3 |
O14—C14—C13 | 124.45 (8) | H231—C23—H232 | 108.0 |
O15—C14—C13 | 112.77 (7) | C23—C24—H241 | 109.5 |
O12—C15—C16 | 104.34 (10) | C23—C24—H242 | 109.5 |
O12—C15—H151 | 110.9 | H241—C24—H242 | 109.5 |
C16—C15—H151 | 110.9 | C23—C24—H243 | 109.5 |
O12—C15—H152 | 110.9 | H241—C24—H243 | 109.5 |
C16—C15—H152 | 110.9 | H242—C24—H243 | 109.5 |
H151—C15—H152 | 108.9 | C212—C211—C216 | 118.46 (8) |
C15—C16—H161 | 109.5 | C212—C211—C217 | 121.42 (8) |
C15—C16—H162 | 109.5 | C216—C211—C217 | 120.12 (7) |
H161—C16—H162 | 109.5 | C211—C212—C213 | 120.55 (9) |
C15—C16—H163 | 109.5 | C211—C212—H21A | 119.7 |
H161—C16—H163 | 109.5 | C213—C212—H21A | 119.7 |
H162—C16—H163 | 109.5 | C214—C213—C212 | 120.72 (10) |
O15—C17—C18 | 107.17 (8) | C214—C213—H21B | 119.6 |
O15—C17—H171 | 110.3 | C212—C213—H21B | 119.6 |
C18—C17—H171 | 110.3 | C213—C214—C215 | 120.60 (10) |
O15—C17—H172 | 110.3 | C213—C214—H21C | 119.7 |
C18—C17—H172 | 110.3 | C215—C214—H21C | 119.7 |
H171—C17—H172 | 108.5 | C214—C215—C216 | 118.38 (10) |
C17—C18—H181 | 109.5 | C214—C215—H21D | 120.8 |
C17—C18—H182 | 109.5 | C216—C215—H21D | 120.8 |
H181—C18—H182 | 109.5 | C215—C216—C211 | 121.28 (9) |
C17—C18—H183 | 109.5 | C215—C216—H21E | 119.4 |
H181—C18—H183 | 109.5 | C211—C216—H21E | 119.4 |
H182—C18—H183 | 109.5 | O23—C217—C211 | 120.27 (8) |
C112—C111—C116 | 118.54 (8) | O23—C217—C22 | 117.57 (7) |
C112—C111—C117 | 121.68 (7) | C211—C217—C22 | 122.01 (7) |
C116—C111—C117 | 119.77 (7) | C31—O32—C33 | 119.08 (7) |
C113—C112—C111 | 120.77 (8) | O31—C31—O32 | 122.23 (8) |
C113—C112—H11A | 119.6 | O31—C31—C32 | 127.29 (8) |
C111—C112—H11A | 119.6 | O32—C31—C32 | 110.48 (8) |
C112—C113—C114 | 119.81 (9) | C32ii—C32—C31 | 117.88 (10) |
C112—C113—H11B | 120.1 | C32ii—C32—C317 | 124.46 (10) |
C114—C113—H11B | 120.1 | C31—C32—C317 | 117.55 (8) |
C115—C114—C113 | 120.05 (9) | O32—C33—C34 | 106.90 (8) |
C115—C114—H11C | 120.0 | O32—C33—H331 | 110.3 |
C113—C114—H11C | 120.0 | C34—C33—H331 | 110.3 |
C116—C115—C114 | 120.37 (9) | O32—C33—H332 | 110.3 |
C116—C115—H11D | 119.8 | C34—C33—H332 | 110.3 |
C114—C115—H11D | 119.8 | H331—C33—H332 | 108.6 |
C115—C116—C111 | 120.43 (8) | C33—C34—H341 | 109.5 |
C115—C116—H11E | 119.8 | C33—C34—H342 | 109.5 |
C111—C116—H11E | 119.8 | H341—C34—H342 | 109.5 |
O16—C117—C111 | 120.74 (8) | C33—C34—H343 | 109.5 |
O16—C117—C12 | 116.22 (8) | H341—C34—H343 | 109.5 |
C111—C117—C12 | 122.82 (7) | H342—C34—H343 | 109.5 |
C122—C121—C126 | 118.99 (8) | C316—C311—C312 | 118.45 (8) |
C122—C121—C127 | 121.17 (8) | C316—C311—C317 | 120.77 (8) |
C126—C121—C127 | 119.83 (7) | C312—C311—C317 | 120.77 (8) |
C123—C122—C121 | 119.81 (8) | C313—C312—C311 | 120.47 (8) |
C123—C122—H12B | 120.1 | C313—C312—H31A | 119.8 |
C121—C122—H12B | 120.1 | C311—C312—H31A | 119.8 |
C124—C123—C122 | 120.97 (9) | C314—C313—C312 | 119.93 (9) |
C124—C123—H12C | 119.5 | C314—C313—H31B | 120.0 |
C122—C123—H12C | 119.5 | C312—C313—H31B | 120.0 |
C123—C124—C125 | 120.89 (9) | C315—C314—C313 | 120.10 (9) |
C123—C124—H12D | 119.6 | C315—C314—H31C | 119.9 |
C125—C124—H12D | 119.6 | C313—C314—H31C | 119.9 |
C126—C125—C124 | 118.97 (9) | C314—C315—C316 | 119.94 (9) |
C126—C125—H12E | 120.5 | C314—C315—H31D | 120.0 |
C124—C125—H12E | 120.5 | C316—C315—H31D | 120.0 |
C125—C126—C121 | 120.36 (8) | C315—C316—C311 | 121.07 (9) |
C125—C126—H12F | 119.8 | C315—C316—H31E | 119.5 |
C121—C126—H12F | 119.8 | C311—C316—H31E | 119.5 |
O13—C127—C121 | 120.40 (8) | O33—C317—C311 | 120.51 (8) |
O13—C127—C13 | 116.54 (8) | O33—C317—C32 | 116.67 (8) |
C121—C127—C13 | 123.00 (8) | C311—C317—C32 | 122.59 (8) |
C15—O12—C11—O11 | 2.31 (14) | C12—C13—C127—C121 | −93.28 (10) |
C15—O12—C11—C12 | −179.96 (8) | C14—C13—C127—C121 | 90.52 (9) |
O11—C11—C12—C13 | 16.95 (12) | C23—O22—C21—O21 | −2.98 (11) |
O12—C11—C12—C13 | −160.70 (7) | C23—O22—C21—C22 | 178.10 (6) |
O11—C11—C12—C117 | −159.99 (8) | O21—C21—C22—C22i | −11.31 (14) |
O12—C11—C12—C117 | 22.36 (10) | O22—C21—C22—C22i | 167.60 (8) |
C11—C12—C13—C127 | 3.82 (10) | O21—C21—C22—C217 | 165.08 (8) |
C117—C12—C13—C127 | −179.50 (7) | O22—C21—C22—C217 | −16.01 (10) |
C11—C12—C13—C14 | 179.93 (6) | C21—O22—C23—C24 | 81.94 (9) |
C117—C12—C13—C14 | −3.39 (10) | C216—C211—C212—C213 | 0.58 (13) |
C17—O15—C14—O14 | −0.64 (10) | C217—C211—C212—C213 | −179.57 (8) |
C17—O15—C14—C13 | 179.04 (6) | C211—C212—C213—C214 | −0.06 (15) |
C12—C13—C14—O14 | −5.58 (11) | C212—C213—C214—C215 | −0.45 (16) |
C127—C13—C14—O14 | 170.79 (7) | C213—C214—C215—C216 | 0.40 (16) |
C12—C13—C14—O15 | 174.74 (6) | C214—C215—C216—C211 | 0.14 (14) |
C127—C13—C14—O15 | −8.89 (9) | C212—C211—C216—C215 | −0.62 (12) |
C11—O12—C15—C16 | 119.76 (10) | C217—C211—C216—C215 | 179.53 (8) |
C14—O15—C17—C18 | −179.22 (7) | C212—C211—C217—O23 | −2.18 (11) |
C116—C111—C112—C113 | −0.13 (11) | C216—C211—C217—O23 | 177.66 (7) |
C117—C111—C112—C113 | −179.10 (7) | C212—C211—C217—C22 | −177.73 (7) |
C111—C112—C113—C114 | −1.49 (13) | C216—C211—C217—C22 | 2.12 (11) |
C112—C113—C114—C115 | 2.23 (14) | C22i—C22—C217—O23 | 89.27 (12) |
C113—C114—C115—C116 | −1.35 (13) | C21—C22—C217—O23 | −86.93 (10) |
C114—C115—C116—C111 | −0.29 (12) | C22i—C22—C217—C211 | −95.08 (12) |
C112—C111—C116—C115 | 1.02 (11) | C21—C22—C217—C211 | 88.73 (10) |
C117—C111—C116—C115 | −179.98 (7) | C33—O32—C31—O31 | −0.30 (12) |
C112—C111—C117—O16 | −1.60 (11) | C33—O32—C31—C32 | −179.56 (7) |
C116—C111—C117—O16 | 179.44 (7) | O31—C31—C32—C32ii | −13.29 (15) |
C112—C111—C117—C12 | 172.80 (7) | O32—C31—C32—C32ii | 165.92 (9) |
C116—C111—C117—C12 | −6.17 (10) | O31—C31—C32—C317 | 163.08 (8) |
C13—C12—C117—O16 | −92.82 (10) | O32—C31—C32—C317 | −17.71 (10) |
C11—C12—C117—O16 | 83.94 (9) | C31—O32—C33—C34 | 163.63 (8) |
C13—C12—C117—C111 | 92.56 (10) | C316—C311—C312—C313 | −0.85 (12) |
C11—C12—C117—C111 | −90.68 (9) | C317—C311—C312—C313 | 179.93 (8) |
C126—C121—C122—C123 | −0.44 (11) | C311—C312—C313—C314 | −0.59 (13) |
C127—C121—C122—C123 | −179.21 (7) | C312—C313—C314—C315 | 1.98 (14) |
C121—C122—C123—C124 | 1.38 (12) | C313—C314—C315—C316 | −1.91 (14) |
C122—C123—C124—C125 | −1.30 (13) | C314—C315—C316—C311 | 0.44 (13) |
C123—C124—C125—C126 | 0.27 (13) | C312—C311—C316—C315 | 0.93 (11) |
C124—C125—C126—C121 | 0.66 (12) | C317—C311—C316—C315 | −179.85 (7) |
C122—C121—C126—C125 | −0.57 (11) | C316—C311—C317—O33 | −0.19 (11) |
C127—C121—C126—C125 | 178.22 (7) | C312—C311—C317—O33 | 179.01 (7) |
C122—C121—C127—O13 | 0.59 (11) | C316—C311—C317—C32 | −174.44 (7) |
C126—C121—C127—O13 | −178.17 (7) | C312—C311—C317—C32 | 4.76 (11) |
C122—C121—C127—C13 | −176.62 (7) | C32ii—C32—C317—O33 | 92.67 (13) |
C126—C121—C127—C13 | 4.62 (11) | C31—C32—C317—O33 | −83.44 (10) |
C12—C13—C127—O13 | 89.41 (10) | C32ii—C32—C317—C311 | −92.88 (12) |
C14—C13—C127—O13 | −86.79 (9) | C31—C32—C317—C311 | 91.01 (10) |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C22H20O6 |
Mr | 380.38 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.828 (6), 15.174 (5), 16.420 (7) |
α, β, γ (°) | 113.52 (3), 99.27 (4), 83.53 (4) |
V (Å3) | 1987.6 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.45 × 0.37 × 0.35 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.941, 0.966 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6828, 6828, 6310 |
Rint | ? |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.017, 0.058, 0.93 |
No. of reflections | 6828 |
No. of parameters | 505 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.32 |
Computer programs: CAD-4-PC (Enraf-Nonius, 1989), TEXSAN (Molecular Structure Corporation, 1989), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.
O11—C11 | 1.1912 (11) | O22—C21 | 1.3156 (10) |
O12—C11 | 1.3082 (12) | O22—C23 | 1.4546 (13) |
O12—C15 | 1.4625 (13) | O23—C217 | 1.2277 (11) |
O13—C127 | 1.2207 (11) | C21—C22 | 1.4590 (14) |
O14—C14 | 1.1990 (11) | C22—C22i | 1.4086 (16) |
O15—C14 | 1.3270 (12) | C22—C217 | 1.4646 (13) |
O15—C17 | 1.4551 (12) | C23—C24 | 1.4996 (14) |
O16—C117 | 1.2219 (11) | C211—C212 | 1.3727 (13) |
C11—C12 | 1.4674 (12) | C211—C216 | 1.3896 (13) |
C12—C13 | 1.3694 (12) | C211—C217 | 1.4637 (12) |
C12—C117 | 1.4681 (14) | C212—C213 | 1.3781 (14) |
C13—C127 | 1.4654 (14) | C213—C214 | 1.3549 (16) |
C13—C14 | 1.4680 (12) | C214—C215 | 1.3858 (16) |
C15—C16 | 1.5017 (18) | C215—C216 | 1.3879 (14) |
C17—C18 | 1.5026 (15) | O31—C31 | 1.2397 (12) |
C111—C112 | 1.3921 (13) | O32—C31 | 1.2965 (11) |
C111—C116 | 1.3926 (12) | O32—C33 | 1.4393 (12) |
C111—C117 | 1.4551 (11) | O33—C317 | 1.2411 (11) |
C112—C113 | 1.3678 (13) | C31—C32 | 1.4603 (13) |
C113—C114 | 1.3848 (15) | C32—C32ii | 1.3970 (17) |
C114—C115 | 1.3712 (15) | C32—C317 | 1.4684 (13) |
C115—C116 | 1.3700 (12) | C33—C34 | 1.4991 (15) |
C121—C122 | 1.3924 (14) | C311—C316 | 1.3857 (12) |
C121—C126 | 1.3970 (12) | C311—C312 | 1.3948 (13) |
C121—C127 | 1.4557 (12) | C311—C317 | 1.4662 (14) |
C122—C123 | 1.3821 (13) | C312—C313 | 1.3868 (15) |
C123—C124 | 1.3494 (14) | C313—C314 | 1.3838 (15) |
C124—C125 | 1.3899 (16) | C314—C315 | 1.3732 (15) |
C125—C126 | 1.3902 (12) | C315—C316 | 1.3842 (15) |
O21—C21 | 1.2223 (11) | ||
C11—O12—C15 | 119.79 (8) | C21—O22—C23 | 117.89 (7) |
C14—O15—C17 | 116.35 (7) | O21—C21—O22 | 123.47 (8) |
O11—C11—O12 | 122.68 (8) | O21—C21—C22 | 124.85 (8) |
O11—C11—C12 | 125.80 (8) | O22—C21—C22 | 111.68 (7) |
O12—C11—C12 | 111.48 (7) | C22i—C22—C21 | 118.61 (9) |
C13—C12—C11 | 119.09 (7) | C22i—C22—C217 | 123.56 (9) |
C13—C12—C117 | 124.49 (8) | C21—C22—C217 | 117.72 (8) |
C11—C12—C117 | 116.34 (7) | O22—C23—C24 | 111.57 (8) |
C12—C13—C127 | 123.61 (8) | C212—C211—C216 | 118.46 (8) |
C12—C13—C14 | 119.42 (7) | C212—C211—C217 | 121.42 (8) |
C127—C13—C14 | 116.86 (7) | C216—C211—C217 | 120.12 (7) |
O14—C14—O15 | 122.78 (8) | C211—C212—C213 | 120.55 (9) |
O14—C14—C13 | 124.45 (8) | C214—C213—C212 | 120.72 (10) |
O15—C14—C13 | 112.77 (7) | C213—C214—C215 | 120.60 (10) |
O12—C15—C16 | 104.34 (10) | C214—C215—C216 | 118.38 (10) |
O15—C17—C18 | 107.17 (8) | C215—C216—C211 | 121.28 (9) |
C112—C111—C116 | 118.54 (8) | O23—C217—C211 | 120.27 (8) |
C112—C111—C117 | 121.68 (7) | O23—C217—C22 | 117.57 (7) |
C116—C111—C117 | 119.77 (7) | C211—C217—C22 | 122.01 (7) |
C113—C112—C111 | 120.77 (8) | C31—O32—C33 | 119.08 (7) |
C112—C113—C114 | 119.81 (9) | O31—C31—O32 | 122.23 (8) |
C115—C114—C113 | 120.05 (9) | O31—C31—C32 | 127.29 (8) |
C116—C115—C114 | 120.37 (9) | O32—C31—C32 | 110.48 (8) |
C115—C116—C111 | 120.43 (8) | C32ii—C32—C31 | 117.88 (10) |
O16—C117—C111 | 120.74 (8) | C32ii—C32—C317 | 124.46 (10) |
O16—C117—C12 | 116.22 (8) | C31—C32—C317 | 117.55 (8) |
C111—C117—C12 | 122.82 (7) | O32—C33—C34 | 106.90 (8) |
C122—C121—C126 | 118.99 (8) | C316—C311—C312 | 118.45 (8) |
C122—C121—C127 | 121.17 (8) | C316—C311—C317 | 120.77 (8) |
C126—C121—C127 | 119.83 (7) | C312—C311—C317 | 120.77 (8) |
C123—C122—C121 | 119.81 (8) | C313—C312—C311 | 120.47 (8) |
C124—C123—C122 | 120.97 (9) | C314—C313—C312 | 119.93 (9) |
C123—C124—C125 | 120.89 (9) | C315—C314—C313 | 120.10 (9) |
C126—C125—C124 | 118.97 (9) | C314—C315—C316 | 119.94 (9) |
C125—C126—C121 | 120.36 (8) | C315—C316—C311 | 121.07 (9) |
O13—C127—C121 | 120.40 (8) | O33—C317—C311 | 120.51 (8) |
O13—C127—C13 | 116.54 (8) | O33—C317—C32 | 116.67 (8) |
C121—C127—C13 | 123.00 (8) | C311—C317—C32 | 122.59 (8) |
C15—O12—C11—O11 | 2.31 (14) | C12—C13—C127—C121 | −93.28 (10) |
C15—O12—C11—C12 | −179.96 (8) | C14—C13—C127—C121 | 90.52 (9) |
O11—C11—C12—C13 | 16.95 (12) | C23—O22—C21—O21 | −2.98 (11) |
O12—C11—C12—C13 | −160.70 (7) | C23—O22—C21—C22 | 178.10 (6) |
O11—C11—C12—C117 | −159.99 (8) | O21—C21—C22—C22i | −11.31 (14) |
O12—C11—C12—C117 | 22.36 (10) | O22—C21—C22—C22i | 167.60 (8) |
C11—C12—C13—C127 | 3.82 (10) | O21—C21—C22—C217 | 165.08 (8) |
C117—C12—C13—C127 | −179.50 (7) | O22—C21—C22—C217 | −16.01 (10) |
C11—C12—C13—C14 | 179.93 (6) | C21—O22—C23—C24 | 81.94 (9) |
C117—C12—C13—C14 | −3.39 (10) | C216—C211—C212—C213 | 0.58 (13) |
C17—O15—C14—O14 | −0.64 (10) | C217—C211—C212—C213 | −179.57 (8) |
C17—O15—C14—C13 | 179.04 (6) | C211—C212—C213—C214 | −0.06 (15) |
C12—C13—C14—O14 | −5.58 (11) | C212—C213—C214—C215 | −0.45 (16) |
C127—C13—C14—O14 | 170.79 (7) | C213—C214—C215—C216 | 0.40 (16) |
C12—C13—C14—O15 | 174.74 (6) | C214—C215—C216—C211 | 0.14 (14) |
C127—C13—C14—O15 | −8.89 (9) | C212—C211—C216—C215 | −0.62 (12) |
C11—O12—C15—C16 | 119.76 (10) | C217—C211—C216—C215 | 179.53 (8) |
C14—O15—C17—C18 | −179.22 (7) | C212—C211—C217—O23 | −2.18 (11) |
C116—C111—C112—C113 | −0.13 (11) | C216—C211—C217—O23 | 177.66 (7) |
C117—C111—C112—C113 | −179.10 (7) | C212—C211—C217—C22 | −177.73 (7) |
C111—C112—C113—C114 | −1.49 (13) | C216—C211—C217—C22 | 2.12 (11) |
C112—C113—C114—C115 | 2.23 (14) | C22i—C22—C217—O23 | 89.27 (12) |
C113—C114—C115—C116 | −1.35 (13) | C21—C22—C217—O23 | −86.93 (10) |
C114—C115—C116—C111 | −0.29 (12) | C22i—C22—C217—C211 | −95.08 (12) |
C112—C111—C116—C115 | 1.02 (11) | C21—C22—C217—C211 | 88.73 (10) |
C117—C111—C116—C115 | −179.98 (7) | C33—O32—C31—O31 | −0.30 (12) |
C112—C111—C117—O16 | −1.60 (11) | C33—O32—C31—C32 | −179.56 (7) |
C116—C111—C117—O16 | 179.44 (7) | O31—C31—C32—C32ii | −13.29 (15) |
C112—C111—C117—C12 | 172.80 (7) | O32—C31—C32—C32ii | 165.92 (9) |
C116—C111—C117—C12 | −6.17 (10) | O31—C31—C32—C317 | 163.08 (8) |
C13—C12—C117—O16 | −92.82 (10) | O32—C31—C32—C317 | −17.71 (10) |
C11—C12—C117—O16 | 83.94 (9) | C31—O32—C33—C34 | 163.63 (8) |
C13—C12—C117—C111 | 92.56 (10) | C316—C311—C312—C313 | −0.85 (12) |
C11—C12—C117—C111 | −90.68 (9) | C317—C311—C312—C313 | 179.93 (8) |
C126—C121—C122—C123 | −0.44 (11) | C311—C312—C313—C314 | −0.59 (13) |
C127—C121—C122—C123 | −179.21 (7) | C312—C313—C314—C315 | 1.98 (14) |
C121—C122—C123—C124 | 1.38 (12) | C313—C314—C315—C316 | −1.91 (14) |
C122—C123—C124—C125 | −1.30 (13) | C314—C315—C316—C311 | 0.44 (13) |
C123—C124—C125—C126 | 0.27 (13) | C312—C311—C316—C315 | 0.93 (11) |
C124—C125—C126—C121 | 0.66 (12) | C317—C311—C316—C315 | −179.85 (7) |
C122—C121—C126—C125 | −0.57 (11) | C316—C311—C317—O33 | −0.19 (11) |
C127—C121—C126—C125 | 178.22 (7) | C312—C311—C317—O33 | 179.01 (7) |
C122—C121—C127—O13 | 0.59 (11) | C316—C311—C317—C32 | −174.44 (7) |
C126—C121—C127—O13 | −178.17 (7) | C312—C311—C317—C32 | 4.76 (11) |
C122—C121—C127—C13 | −176.62 (7) | C32ii—C32—C317—O33 | 92.67 (13) |
C126—C121—C127—C13 | 4.62 (11) | C31—C32—C317—O33 | −83.44 (10) |
C12—C13—C127—O13 | 89.41 (10) | C32ii—C32—C317—C311 | −92.88 (12) |
C14—C13—C127—O13 | −86.79 (9) | C31—C32—C317—C311 | 91.01 (10) |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y+2, −z+1. |
The title compound, (I), is a member of the lignans, which are natural products. Because of its broad range of biological activities (Macrae et al., 1984), limited deposition in nature and complicated stereochemistry, much interest has been focused on it (Knorr, 1896; Pelter et al., 1982; Wu et al., 1997). Many consider it to be formed by dimerization of an ArC3 fragment at the β,β-C atoms through a single bond and the β-C atoms are chiral (Wu et al. 1997). In order to deepen the understanding of the structure of the title compound at a molecular level and to provide some information on the synthesis of this class of organic compounds, we determined the crystal structure. We found that the title compound does not have chiral C atoms; the two β-C atoms (C12 and C13) are joined by a double bond of length 1.3694 (12) Å and the sums of the bond angles at C12 and C13 are 359.92 (7) and 359.89 (7)°, respectively. Two benzene rings, lying on different sides of the diethyl 2-butenedioate main chain, are almost parallel to each other and nearly perpendicular to the main chain. In the unit cell, one molecule lies in a general position, with its inversion-related partner, and two molecules lie on inversion centres.